She is self-confident and secure about her relationship with Max despite finding out about their past history. Naomi keeps trying to dig up dirt on her, but she fails every time, with even her own friends stating that Madison is an "angel".

At her bachelorette party, Madison has too much to drink and tries to free a shark from a fish tank before being arrested by the cops, which causes Naomi to feel guilty. Madison swears never to drink again.

However, at the wedding, Naomi comes through the door and declares her love for Max, resulting in a silent church. Naomi scoots out the back and tells them to carry on, but Max calls off the wedding and reunites later with Naomi.

In season 5, Naomi goes to Madison when she begins having trouble with Alec Martin, who keeps interfering in her relationship. Madison tells her that Alec was the one who recommended Madison hire Naomi as her wedding planner and Naomi informs her that Alec did it to wreck their relationship. She asks for Madison's help for Max's sake.

Madison comes with Naomi to see Max, but Madison gets really drunk and is caught between Naomi and Alec as they both argue their case.